Tell me, do most of the trackdays you go to are well organised, like do they try and match up driver and car abilities or is it a free for all. In the latter the chance of someone pulling out into a quicker car's path is much greater and accidents are sure to occur.

I track with BMW CCA, so things are "relatively" safe in those events. But you can still run out of road or spin the car if you push things beyond the car's/your limit obviously, which is what I would like to hedge against. And of course there is the freak accident that is caused by fluid leak on the track, etc. If the quote does indeed cover multiple days at the same event, $250 for 2-3 days sounds very reasonable to me and I would take it for the peace of mind.